The Grateful Dead was one of the most influential rock bands of the latter half of the 20th century. Formed in 1965, the group became known for its unique musical style, which took inspiration from folk, bluegrass, rock, and more. These 15 songs are some of the most iconic of their 30-year existence.
1. Fire On The Mountain
Fire On The Mountain was already a staple of the Grateful Dead’s live performances when it was recorded in 1978. The song had undergone several edits and usually involved extensive live improvisations during shows; in fact, some performances included different lyrics or new verses until the band cultivated a final draft. The song was typically paired with Scarlet Begonias; between the two songs, the performance often lasted close to 30 minutes.
After the release of Fire On The Mountain, the Grateful Dead continued performing it regularly during their live shows until they disbanded in 1995. The song has been covered extensively in a variety of genres, including bluegrass and country.
Next: The top rock songs of the ’70s (our full list)
2. Uncle John’s Band
The Grateful Dead first began playing Uncle John’s Band in 1969; it was recorded for their 1970 album Workingman’s Dead. The song, inspired by bluegrass and folk music, featured largely acoustic instruments; it was praised for its layered vocal harmonies. Its musical and lyrical accessibility made it popular with fans, and it remains one of the band’s best-known songs.
Many of the lyrics refer to other songs by the Grateful Dead or to local Appalachian folk sayings or practices. There are also extensive references to American nationalism and military might, which were highly relevant topics in the wake of the War in Vietnam. The Rock & Roll Hall of Fame has named Uncle John’s Band on its list of 500 Songs That Shaped Rock And Roll.
Next: Greatest rock genre albums ever recorded
3. Touch Of Grey
![Grateful Dead - Touch Of Grey (Official Music Video) [HD]](https://www.musicgrotto.com/wp-content/plugins/wp-youtube-lyte/lyteCache.php?origThumbUrl=https%3A%2F%2Fi.ytimg.com%2Fvi%2Fmzvk0fWtCs0%2F0.jpg)
The Grateful Dead released Touch Of Grey in 1987, making it a feature of their later years as a group. The track was a huge success, placing in the top 10 on both the Billboard Hot 100 and the Mainstream Rock Airplay chart (it reached No. 1 on the latter).
The accompanying music video was also a hit on MTV and has become one of the most iconic videos of the decade; it features the band members as skeleton versions of themselves, performing the song to a room full of fans. The skeletons are revealed to be operated by the living musicians, who are operated like marionettes by two giant skeletal hands. The making of the song and music video were later shared in the documentary Dead Ringers: The Making of the Touch of Grey Video.
Next: Top rock songs of the 1980s (full list)
4. Dark Star
Dark Star was released in the 1960s during a time when the Grateful Dead was experimenting with genres such as psychedelic rock and acid rock. It was a frequent feature of live jam sessions, which the band usually performed during their shows.
The lyrics were inspired by the poem The Love Song Of J. Alfred Prufrock by T.S. Eliot, which are paraphrased in the verses. The song consisted of two short verses exploring themes of life, death, and rebirth; extended instrumental passages usually followed them. These ambiguous lyrics have been extensively analyzed by fans over the years, prompting discussion as to what they really mean.
The truth, as shared by songwriter Robert Hunter? Some of the lyrics have a deeper meaning, while some are simply based on what he thought sounded good at the time.
5. Bertha
The song Bertha appeared on the Grateful Dead’s untitled 1971 album, famously called The Skull & Roses album. It was noted for its strange, even silly lyrics, many of which are bizarre or hard to understand. Bertha is an elaborate metaphor for death and rebirth, with a pun on the name “Bertha” and the word “birth.” The song follows an unnamed character as they travel from place to place to get out of the rain; they are also searching for Bertha, either a person or a concept—or perhaps both.
Grateful Dead fans consider Bertha to be an essential part of the Grateful Dead’s legacy. It belongs to the era of Grateful Dead songs that explore the old, forgotten corners of rural American culture, the vestiges of which can be seen in bluegrass and folk music.
6. Box Of Rain
Box Of Rain, released in 1970, was a departure from the band’s usual sound; in fact, the composer explicitly didn’t want it to sound “like a Grateful Dead song.” In light of this, they swapped out their usual guitars for acoustic piano. Bassist Phil Lesh, who composed the melody, requested that the lyrics be suitable for him to sing to his ailing father, who was dying of cancer. The result was Box Of Rain, which became one of their best-known songs.
The title itself was intended to be a description of the world. Lesh provided the vocals for the song, which became a favorite of fans. Audiences would often yell “Let Phil sing!” to request the song during concerts. It was also the last song the band performed live during their final performance in July 1995.
Next: Greatest guitar solos of all time feature
7. Truckin’
The Grateful Dead released Truckin‘ in 1970. The song, which uses classic blues and folk instrumentalization, tells the story of the drug raid on the band members’ hotel while they were on tour in New Orleans. The raid led to the arrest of 19 people, including three members of the band, some of their crew, and many fans.
The band members paid bail for all those arrested. The story gained national attention, with tabloids fixating on the drug charges (which included LSD). Truckin’ was released later that year and became one of the most widely-played songs of their live shows. In 1997, the United States Library of Congress categorized the song as an artistic work that was culturally and historically significant.
Next: The top folk songs of all time list
8. Eyes Of The World
The Grateful Dead released Wake Of The Flood in 1973, their first studio album in three years and the first without Ron McKernan. The album signaled a transition to jazz-inspired rock with elements of folk and R&B rather than the older blues-heavy music.
One of the album’s tracks was Eyes Of The World, a peace-and-love song about unifying the world. The lyrics, which have sometimes been considered a bit too on-the-nose in terms of hippie sentiment, were strongly inspired by the writings of philosopher Blaise Pascal.
Though Eyes Of The World didn’t chart, Wake Of The Flood was the band’s first significantly popular album of the decade and the song became a fixture at live performances. It has been estimated that, of the 381 times the song was performed live, 49 of those performances took place in 1973 alone.
9. Shakedown Street
The Grateful Dead’s 1978 album Shakedown Street was poorly received by critics, who said that the recording quality was poor and slapdash. Nevertheless, the title song from the album went on to be successful, and the phrase “Shakedown Street” even became used by fans to refer to the places outside concert arenas where band merchandise was sold. It has gone on to refer to the same phenomenon outside any concert venue, not just where the Grateful Dead was playing.
Despite the criticism, the album reached No. 41 on the Billboard Top 200 the year after its release. Shakedown Street became a fixture of the band’s concerts, often serving as their opening song. It was marked for its disco-infused musicality, which was frequently slowed to a smoother R&B feel when played onstage.
10. Scarlet Begonias
Scarlet Begonias was released in 1974. The song was about meeting a potential lover and comparing the initial flirtation to gambling with matches. Like many other Grateful Dead songs, the song also prompts meditations on larger questions of life and spirituality.
There are many references to other songs, folk tales, and works of literature in the lyrics. These include the novel The Wind In The Willows as well as classic English folk songs, which often open with the lyrics “As I was walking.”
Scarlet Begonias became a favorite of Grateful Dead fans and was a fixture at live performances. During concerts, it was frequently combined with Fire On The Mountain as a medley, which the band referred to as Scarlet Fire. The two songs together often included extensive improvisational passages and took anywhere from 25 to 34 minutes to play.
11. Ripple
Ripple was featured on the Grateful Dead’s 1970 album American Beauty and was released alongside Truckin’. The song was the result of a prolific afternoon of composition by Grateful Dead member Robert Hunter, during which he reportedly drank half a bottle of fortified wine.
The song is one of the band’s best-known tracks. The complex lyrics have led to decades of analysis, with some writing essays about it. Hunter himself said that it was one of the songs he was proudest of, particularly the line “Let it be known that there is a fountain/That was not made by the hands of men.”
The mournful melody was composed while the band was on tour, on a stop during their train journey. It was recorded in stunningly sweet, layered vocal harmonies that have made Ripple one of the Dead’s most iconic songs.
12. Friend Of The Devil
The Grateful Dead first introduced their track, Friend Of The Devil, during one of their live performances in 1970. As with many of their songs, it became a staple of concerts before the band recorded it. They spent these concerts improvising and trying out different variations before finally releasing it on their album American Beauty later that year.
The song is an acoustic bluegrass track, though performances in the mid-1970s incorporated a slower tempo with longer instrumental solos. It has become widely known for its distinctive guitar riff.
Friend Of The Devil also bears the title of the most covered song by the Grateful Dead. Notably, it has been adapted by Counting Crows, Tom Petty, Bob Dylan, Loggins & Messina, Elvis Costello, Mumford & Sons, and Dave Matthews Band. In this way, Hunter has said, it is the band’s closest thing to a classic.
13. Casey Jones
![Grateful Dead - Casey Jones (2020 Remaster) [Official Audio]](https://www.musicgrotto.com/wp-content/plugins/wp-youtube-lyte/lyteCache.php?origThumbUrl=https%3A%2F%2Fi.ytimg.com%2Fvi%2Fd160GSGtPxY%2F0.jpg)
The Grateful Dead released Casey Jones in 1970 on their album, Workingman’s Dead. The song tells the story of Casey Jones, a train operator who got into a fateful crash in April 1900. The band’s version, however, is slightly embellished, with the detail that Jones was “high on cocaine.”
This was not historically accurate, but the song became widely known for the lyrics and was one of their most enduring pieces. Originally in a blues rock setting, it has been covered many times in various genres. It is also one of the best-known songs outside the band’s fanbase, as it was frequently played on alternative and progressive rock stations.
14. St. Stephen
St. Stephen was one of the Grateful Dead’s earliest hits. It was released on their 1969 album Aoxomoxoa and was a staple of their concerts until the 1970s. The title comes from the story of St. Stephen, the first Christian martyr, who was stoned to death for his faith.
The band moved away from regularly performing it by the early 1970s, when they changed from their usual psychedelic rock. Crowds continued to request it regularly until the group disbanded.
15. Sugar Magnolia
Sugar Magnolia is one of the band’s best-known songs, released in 1970 on American Beauty. It has been estimated that it was the second-most-often played song in their concerts, following Me & My Uncle
It was also famous for its two distinct parts, the main Sugar Magnolia and the coda known as Sunshine Daydream. When the song was performed live, there was often a break between the sections. It lasted a few beats or even a few songs. On some occasions, it lasted several days.
As the Head Editor and Writer at Music Grotto, Liam helps write and edit content produced from professional music/media journalists and other contributing writers. He works closely with journalists and other staff to format and publish music content for the Music Grotto website. Liam is also the founding member of Music Grotto and is passionate in disseminating editorial content to its readers.
Liam’s lifelong love for music makes his role at Music Grotto such a rewarding one. He loves researching, writing and editing music content for Music Grotto.
